Reactions of a N-Acyliminium Ion Pool with Benzylsilanes. Implication of a Radical/Cation/Radical Cation Chain Mechanism Involving Oxidative C−Si Bond Cleavage

The reaction of a N-acyliminium ion pool with benzylsilane proceeds by a chain mechanism involving oxidative C−Si bond cleavage. A radical/cation/radical cation crossover mechanism involving single electron transfer has been proposed. The effective binary system consisting of a stoichiometric amount of a benzylsilane and a catalytic amount of a more easily oxidized benzylstannane has been developed.